Reactome | Vinyl chloride is oxidized to 2-Chloroethylene oxide

Vinyl chloride is oxidized to 2-Chloroethylene oxide

Stable Identifier

R-HSA-76354

Type

Reaction [transition]

Species

Homo sapiens

Compartment

smooth endoplasmic reticulum

ReviewStatus

5/5

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Metabolism (Homo sapiens)

- Biological oxidations (Homo sapiens)
  - Phase I - Functionalization of compounds (Homo sapiens)
    - Cytochrome P450 - arranged by substrate type (Homo sapiens)
      - Xenobiotics (Homo sapiens)
        
        CYP2E1 reactions (Homo sapiens)
        
        Vinyl chloride is oxidized to 2-Chloroethylene oxide (Homo sapiens)

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Vinyl chloride is oxidized to 2-Chloroethylene oxide

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CYP2E1 can catalyze the oxidation of the vinyl halide vinyl chloride to the epoxide 2-chloroethylene oxide. The epoxide is very unstable and rearranges quickly to 2-chloroacetaldehyde. Both these products can interact with DNA and proteins.

Literature References

PubMed ID	Title	Journal	Year
1664256	Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects Kim, DH, Iwasaki, M, Guengerich, FP	Chem Res Toxicol	1991
497175	Activation of vinyl chloride to covalently bound metabolites: roles of 2-chloroethylene oxide and 2-chloroacetaldehyde Watanabe, PG, Guengerich, FP, Crawford, WM Jr	Biochemistry	1979